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  • Gift Badge For Jos. A. Bank Chelsea Boots
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    The regular price is   $145.00 The sale price is   $108.75 sale

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    Description:
    For a refined yet versatile footwear option, consider the Joseph Abboud Beaumont Suede Chelsea Boots from Jos. A. Bank. Crafted from soft suede, these boots feature elastic side gores for easy slip-on and removal, ensuring both style and convenience. The tapered toe design and welt profile provide a modern silhouette that pairs effortlessly with both chinos and casual denim.
  • Gift Badge For Moretti Zion Lace-Up Boots
    The regular price is   $130.00 The sale price is   $97.50 sale

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    Description:
    Step into refined style with these boots from Moretti. Crafted from premium leather, they offer a sophisticated and durable design that seamlessly transitions from the office to weekend outings. The lace-up closure provides a secure fit, while the sturdy construction ensures long-lasting comfort and support, no matter where your day takes you.
  • Gift Badge For Vintage Foundry Randall Chelsea Boots
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    The regular price is   $130.00 The sale price is   $97.50 sale

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    Description:
    This refined Chelsea boot blends rugged style with everyday ease. Made with a leather upper and stretch gore panels, it slips on effortlessly while offering a secure fit. The almond toe and stacked heel give it a sharp, versatile profile. A leather lining adds comfort, and the durable rubber outsole provides traction. A versatile footwear option, you can dress it up or down.
  • Gift Badge For Vintage Foundry Flint Dress Boots
    The regular price is   $200.00 The sale price is   $150.00 sale

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    Description:
    Known for vintage-inspired craftsmanship, Vintage Foundry Co. designs balance timeless detail with modern wearability. The Flint pairs classic style with standout texture. Made from a combination of leather and cotton, it features a two-tone herringbone pattern with a wool-like finish for a refined yet distinctive look. A pull tab and rubber outsole add function.
  • Gift Badge For Vintage Foundry Evans Chelsea Boots
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    The regular price is   $125.00 The sale price is   $93.75 sale

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    Description:
    Effortlessly cool and undeniably versatile, this Chelsea boot is crafted from premium suede with elastic side panels for easy on and off. The streamlined silhouette and stacked heel offer a refined finish that works just as well with jeans as it does with tailored trousers. With a rugged yet polished feel, it's a modern essential for any well-rounded wardrobe.
  • Gift Badge For Vintage Foundry Martin Chelsea Boots
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    The regular price is   $120.00 The sale price is   $90.00 sale

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    Description:
    Rugged and built for everyday wear, this Chelsea boot brings together timeless style and dependable comfort. The elastic side panels and pull tab make it easy to slip on and go, while the durable sole adds traction and longevity. Whether you're dressing up or keeping it casual, it's a refined finish to your look.
  • Gift Badge For Eastland Allagash Standard Plain Toe Boots
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    The regular price is   $145.00 The sale price is   $108.75 sale

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    Description:
    Take the rugged road in stride with these Eastland boots crafted from full-grain leather. Equal parts sturdy and stylish, they're your all-season sidekicks, offering comfort and classic charm. Crafted for durability with a plain toe design, they walk the fine line between polished and laid-back. Whether you're tackling city streets or weekend getaways, these boots stay ready to roll. Lace up, step out, and let them carry you wherever adventure calls. They're a versatile win for your casual wardrobe upgrade.
  • Gift Badge For Eastland Jack Chukka Ankle Boots
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    The regular price is   $125.00 The sale price is   $93.75 sale

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    Description:
    Built for everyday versatility, this chukka boot features a full-grain leather upper that adds a rich, polished finish to casual and business-casual looks alike. The durable, super lightweight rubber and EVA combo outsole delivers comfort without the bulk, making it ideal for long days on your feet. Pair it with slim-fit jeans and a Henley for a relaxed weekend vibe, or style it with tailored trousers and a sport coat for a modern office-ready ensemble.
  • Gift Badge For Eastland Chimney Pond Chelsea Boot
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    The regular price is   $145.00 The sale price is   $108.75 sale

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    Description:
    Step into effortless style with these boots from Eastland. Designed for the modern man who values both versatility and comfort, they feature a timeless plain toe look that pairs as easily with your office wardrobe as it does with your weekend denim. The elastic side panels and pull tab make slipping them on a breeze. Built with durable leather and a sturdy sole, they're ready to wander wherever you're headed. Whether it's coffee runs or a night on the town, these boots keep you grounded in style.
  • Gift Badge For Eastland Daily Double Pull On Boots
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    The regular price is   $125.00 The sale price is   $93.75 sale

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    Description:
    With a smooth leather upper that's easy to care for, this pull-on boot delivers everyday polish with minimal effort. The Active Memory Foam comfort insole cushions each step, while the flexible TPR outsole moves with you for all-day wearability. Slip it on with slim jeans and a utility jacket for a casual, go-anywhere look, or pair it with khakis and a sweater for a laid-back office outfit.
  • Gift Badge For Ben Sherman Whitby Chukka Boots
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    The regular price is   $70.00 The sale price is   $52.50 sale

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    Description:
    Crafted for everyday wear, the Whitby chukka delivers a modern take on a timeless favorite. Its smooth synthetic leather upper pairs effortlessly with both jeans and chinos, while the lightweight EVA outsole adds a sporty edge. With a cushioned insole and breathable lining, it's built for comfort without compromising style.
  • Gift Badge For Johnston & Murphy Calder Chelsea Boots
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    The sale price is   $179.00
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    Description:
    The Calder boot brings together versatile design and everyday functionality. Crafted from rich leather, they feature elastic side panels and a pull tab for easy on-and-off wear. A natural fit for both dressier occasions and casual outings, this pair features a cushioned footbed and soft lining for lasting comfort. The durable outsole offers reliable traction. Pair them with denim, chinos, or tailored trousers for effortless style you can rely on.
  • Gift Badge For Johnston & Murphy Calder Chukka Boots
    New
    The sale price is   $179.00
    Description:
    Bridging rugged charm and refined style, the Johnston & Murphy Calder Chukka Boots are a versatile staple for a modern wardrobe. Crafted from premium leather, these ankle-high boots have subtle stitching and a classic lace-up design. The cushioned footbed and soft lining provide all-day comfort, while the durable outsole offers reliable traction on a variety of surfaces.
  • Gift Badge For Johnston & Murphy Braxton Chukka Boots
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    The sale price is   $159.00
    Description:
    The Braxton chukka boot is crafted from rich leather with subtle stitched details. Designed for flexibility and durability, they have a cushioned footbed and sturdy outsole that provide support whether you're heading to the office or exploring the city. The ankle-high profile delivers a tailored look that pairs effortlessly with denim, chinos, or even casual suiting, making it a go-to choice for transitional dressing and year-round wear.
  • Gift Badge For Florsheim Plain Toe Chukka Boots
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    The sale price is   $135.00
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    Description:
    Polished yet practical, these Florsheim chukka boots deliver everyday versatility with a refined edge. Crafted from rich leather and set on a durable rubber sole, it pairs classic chukka styling with modern comfort features. A cushioned footbed and soft Suedetec lining provide support from morning commutes to evening plans, while the clean plain toe keeps your look sharp. Whether you're dressing up denim or adding a relaxed touch to tailored trousers, this boot moves effortlessly through the week.
  • Gift Badge For Stacy Adams Brumley Moc Toe Lace Up Boots
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    The sale price is   $160.00
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    Description:
    Rugged meets refined in the Brumley boot, a versatile style from the brand's FlexZone collection. Featuring a rich, hand-burnished upper with a modern mix of materials, colors, and textures, this boot is designed for both visual impact and all-day comfort. The FlexZone cushioned footbed includes a molded heel cup and sustainable microfiber cover, offering anatomical arch support that adapts to your stride. Soft microfiber linings enhance comfort, while the lace-up design and moc toe silhouette add a classic touch to a contemporary silhouette.
  • Gift Badge For Stacy Adams Townsend Plain Toe Chelsea Boots
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    The sale price is   $150.00
    Description:
    Modern and versatile, the Stacy Adams Townsend boot is crafted from rich tumbled leather with gore panels for easy on-and-off wear. It pairs effortlessly with both casual and dress looks, while the RedZone cushioned footbed provides anatomical arch support and a molded heel cup for enhanced comfort. A lightweight sole adds flexibility and durability, making this Chelsea boot a reliable choice for everyday style with a refined edge.
  • Gift Badge For Jos. A. Bank Dress Chelsea Boots
    New
    The regular price is   $145.00 The sale price is   $108.75 sale

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    Description:
    Timeless and versatile, these classic leather Chelsea boots add polish to your wardrobe. Featuring clean lines, elastic side gores, and a streamlined silhouette, they slip on easily and pair effortlessly with both tailored looks and casual denim. Crafted from smooth leather, they offer durability, comfort, and refined style in equal measure.
  • Gift Badge For Florsheim Forge Plain Toe Chukka Boots
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    The sale price is   $130.00
    Description:
    A smooth leather upper and stacked heel give this chukka boot a versatile, stylish look, while breathable textile linings add all-day ease. The removable footbed features OrthoLite high-rebound foam and a molded EVA heel cup for superior cushioning and support. A durable rubber outsole completes the design, offering reliable traction with every step.
  • Gift Badge For Florsheim Lodge Chukka Boots
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    The sale price is   $140.00
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    Description:
    An instant classic, these Florsheim chukka Boots blend smooth leather with modern stitching and a cool stacked heel. Its versatile design pairs effortlessly with chinos or jeans, making it your go-to for countless occasions. Inside, you'll find soft, comfortable Suedetec linings and a fully cushioned footbed with Ortholite high-rebound foam for exceptional all-day comfort, all supported by a durable rubber sole.
  • Gift Badge For Jos. A. Bank Pebbled Leather Chukka Boots
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    The regular price is   $140.00 The sale price is   $105.00 sale

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    Description:
    For a versatile and stylish addition to your footwear collection, consider the leather chukka boots from Jos. A. Bank. Crafted with a rich leather upper, they offer a timeless appeal suitable for various occasions. The classic silhouette is enhanced with a durable lug sole, providing added traction and making them ideal for navigating unpredictable weather or exploring off-the-beaten-path. Whether paired with chinos for a polished look or jeans for a more casual ensemble, these boots are designed to elevate your style effortlessly.
  • Gift Badge For Jos. A. Bank Chukka Boots
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    The regular price is   $140.00 The sale price is   $105.00 sale

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    Description:
    Refined yet rugged, this Jos. A. Bank chukka boot strikes the perfect balance between polish and versatility. Crafted from smooth leather with classic eyelet styling, it's designed for comfort and easy pairing from tailored trousers to your favorite jeans. A timeless staple built for seasons of wear.
  • Gift Badge For Stacy Adams Henry Cap Toe Lace Boots
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    The sale price is   $165.00
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    Description:
    A modern take on a classic silhouette, the Henry boot is perfect for elevating your professional or casual style. Crafted with a polished upper and a distinctive cap-toe design, this boot offers a refined look that's both timeless and on-trend. The secure lace-up closure and durable stacked heel provide both a comfortable fit and lasting quality. Whether you pair it with a tailored suit or with dark denim, it's a versatile staple for your wardrobe.
  • Gift Badge For Florsheim Forge Plain Toe Chelsea Boots
    Online Exclusive
    The sale price is   $130.00
    Description:
    Made with a smooth leather upper and a modern stacked heel, this Florsheim boot slips on easily thanks to flexible side gore panels. Inside, a breathable textile lining and cushioned, removable footbed with OrthoLite high-rebound foam, and a molded EVA heel cup deliver lasting support. A durable rubber outsole rounds out the design, offering reliable traction for workdays and weekends alike.